通过离子液体催化的氮杂迈克尔加成反应合成16α-氨基孕烯醇酮衍生物及其作为C-裂解酶抑制剂的评价

Synthesis of 16α-amino-pregnenolone derivatives via ionic liquid-catalyzed aza-Michael addition and their evaluation as C-lyase inhibitors.

作者信息

Szánti-Pintér Eszter, Maksó Lilla, Gömöry Ágnes, Wouters Johan, Edina Herman Bianka, Szécsi Mihály, Mikle Gábor, Kollár László, Skoda-Földes Rita

机构信息

University of Pannonia, Institute of Chemistry, Department of Organic Chemistry, Egyetem u. 10 (P.O. Box 158), H-8200 Veszprém, Hungary.

Hungarian Academy of Sciences, Research Centre for Natural Sciences, Magyar tudósok körútja 2, H-1117 Budapest, Hungary.

出版信息

Steroids. 2017 Jul;123:61-66. doi: 10.1016/j.steroids.2017.05.006. Epub 2017 May 11.

DOI:10.1016/j.steroids.2017.05.006

PMID:28502863

Abstract

Aza-Michael addition of 16-dehydropregnenolone was studied in the presence of a basic ionic liquid, [DBU][OAc] as catalyst and solvent. The reaction was carried out using different primary and secondary amines as N-nucleophiles. The products were obtained in moderate to good yields and were characterized by H and C NMR, MS and IR. The ionic liquid was found to be an efficient and recyclable catalyst that was reused five times. The products were investigated for the inhibition of in vitro C-lyase activity and displayed moderate inhibitory effect.

摘要

在碱性离子液体[DBU][OAc]作为催化剂和溶剂的存在下，研究了16-脱氢孕烯醇酮的氮杂迈克尔加成反应。使用不同的伯胺和仲胺作为N-亲核试剂进行反应。产物以中等至良好的产率得到，并通过氢谱、碳谱、质谱和红外光谱进行表征。发现该离子液体是一种高效且可循环使用的催化剂，可重复使用五次。对产物进行了体外C-裂解酶活性抑制研究，结果显示出中等程度的抑制作用。